Synthetic polymers are used in a wide variety of applications. In many applications, these synthetic polymers are crosslinked in order to achieve the required performance properties. For over 60 years, a large class of commercially important thermoset polymers have utilized formaldehyde-based crosslinking agents. Such crosslinking agents based on formaldehyde traditionally have provided an efficient and cost-effective means of curing a wide variety of materials. Examples of formaldehyde-based crosslinking agents include melamine-formaldehyde, urea-formaldehyde, phenol-formaldehyde and acrylamide-formaldehyde adducts. With growing toxicity and environmental concerns, there has been an ongoing search to replace formaldehyde-based crosslinking agents. However, these alternative crosslinkers have suffered from significant deficiencies including low or slow cure, requiring end uses to change their commercial high speed application equipment, emission of toxic components or volatile organic compounds other than formaldehyde.
A particularly attractive crosslinking reaction involves the esterification of a carboxylic acid functional polymer with a hydroxyl functional polymer. This is an attractive reaction since water is the only product of the crosslinking reaction. However, for polymeric systems, this reaction is difficult to conduct effectively since it is slow under conventional time and temperature conditions of cure. Raising the temperature to force this curing reaction results in unacceptable color development and/or degradation, with the emission of unwanted volatile organic compounds.
.beta.-Hydroxyalkyl amide functionality was developed to facilitate the esterification crosslinking of carboxylic acid containing polymers. However, this technology still is deficient in crosslinking rate and crosslinking densities under conditions typically used for formaldehyde based crosslinking agents. In addition to the high temperature and long curing time requirements for crosslinking, the use of a catalyst is only marginally effective in accelerating the reaction of .beta.-hydroxyl amides.
To address this unfilled need for a formaldehyde-free crosslinker, we have found unexpectedly that (hydroxyalkyl)urea derivatives result in facile and safe crosslinking of di- and/or poly-functionalized molecules and polymers, as described herein below.